Hydrochloric Acid → 4-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl Ester

HRID 989411

Reaction equation

HRID 989411 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:12])[C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][O:6][C:5](=[O:7])[C:4]1[CH:3]=[C:2]([I:1])[C:10]([O:11][CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=2)=[C:9]([I:12])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 12065Ioxynic acidHCID 699793-Bromobenzyl bromide

Product 1

HCID 121488754-(3-Bromobenzyloxy)-3,5-diiodo-benzoic Acid 3-bromobenzyl EsterYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3,5-diiodo-4-hydroxybenzoic acid (0.39 g, 1.0 mmol), 3-bromobenzyl bromide (0.62 g, 2.5 mmol), and cesium carbonate (0.98 g, 3.0 mmol) in 10 mL DMF was stirred for 15 hours at room temperature. The mixture was then poured into 1 M HCl (100 mL) and a white precipitate formed. The precipitate was isolated by vacuum filtration and was recrystallized from hot isopropanol/chloroform, yielding the title compound as bright white crystals (610 mg, 84%); 1H NMR (CDCl3) δ 8.48 (s, 2H), 7.80 (br. s, 1H), 7.58-7.49 (m, 4H), 7.38-7.28 (m, 3H), 5.31 (s, 2H), 5.01 (s, 2H).

Workup

  1. customa white precipitate formed
  2. customThe precipitate was isolated by vacuum filtration
  3. customwas recrystallized from hot isopropanol/chloroform

Sources & evidence

ORD record
ord-9fe9c7e04bdd46bdb323e1cb45c9fdca
Source dataset
uspto-grants-2003_10
Patent number
US06638977B1

Linked notes

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